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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 4| April 2009| Pages o734-o735
doi:10.1107/S160053680900806X

Methyl 3-hydr­­oxy-4-(3-methyl­but-2-en­yl­oxy)benzoate

Mei-yan Wei,a Zhen Liu,b Xiu-li Zhang,c Chang-lun Shaoc and Chang-yun Wangc*

aSchool of Pharmacy, Guangdong Medical College, Dongguan, Guangdong 523808, People's Republic of China, bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang, Henan 471022, People's Republic of China, and cSchool of Medicine and Pharmacy, Ocean University of China, Qingdao, Shandong 266003, People's Republic of China
*Correspondence e-mail: changyun@ouc.edu.cn

(Received 16 February 2009; accepted 5 March 2009; online 11 March 2009)

The title compound, C13H16O4, was isolated from culture extracts of the endophytic fungus Cephalosporium sp. The ester and ether substituents are twisted only slightly out of the benzene ring plane, making dihedral angles of 2.16 (2) and 3.63 (5)°, respectively. The non-H atoms of all three substituents are almost coplanar with the benzene ring, with an r.m.s. deviation of 0.0284 Å from the mean plane through all non-H atoms in the structure. A weak intra­molecular O—H⋯O hydrogen bond contributes to this conformation. In the crystal structure, mol­ecules are linked into a one-dimensional chain by inter­molecular O—H⋯O hydrogen bonds. Weak non-classical C—H⋯π contacts are also observed in the structure.

Related literature

For structures with C—H⋯O and C—H⋯π contacts, see: Nangia (2002[Nangia, A. (2002). CrystEngComm, 4, 93-101.]); Umezawa et al. (1999[Umezawa, Y., Tsuboyama, S., Takahashi, H., Uzawa, J. & Nishio, M. (1999). Bioorg. Med. Chem. 7, 2021-2026.]). For new bioactive secondary metabolites from the endophytic strain B60, see: Shao et al. (2007[Shao, C. L., Guo, Z. Y., Peng, H., Peng, G. T., Huang, Z. J., She, Z. G., Lin, Y. C. & Zhou, S. N. (2007). Chem. Nat. Compd, 43, 377-379.], 2008[Shao, C. L., Hu, G. P., Zhang, X. L., Wang, C. Y., She, Z. G. & Lin, Y. C. (2008). Acta Sci. Nat. Univ. Sunyatseni, 47, 133-134.]). For an investigation of the endophytic fungus, see: Shao et al. (2008[Shao, C. L., Hu, G. P., Zhang, X. L., Wang, C. Y., She, Z. G. & Lin, Y. C. (2008). Acta Sci. Nat. Univ. Sunyatseni, 47, 133-134.]). For a related structure, see: Huang et al. (2005[Huang, H.-R., Feng, X.-L., She, Z.-G., Lin, Y.-C., Vrijmoed, L. L. P. & Jones, E. B. G. (2005). Acta Cryst. E61, o282-o283.]).

[Scheme 1]

Experimental

Crystal data

  • C13H16O4

  • Mr = 236.26

  • Triclinic, [P \overline 1]

  • a = 7.8401 (16) Å

  • b = 8.3899 (17) Å

  • c = 11.099 (2) Å

  • α = 100.655 (3)°

  • β = 98.771 (3)°

  • γ = 115.456 (3)°

  • V = 625.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 291 K

  • 0.40 × 0.38 × 0.35 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.964, Tmax = 0.968

  • 4817 measured reflections

  • 2420 independent reflections

  • 2058 reflections with I > 2σ(I)

  • Rint = 0.014
Refinement

  • R[F2 > 2σ(F2)] = 0.051

  • wR(F2) = 0.161

  • S = 1.05

  • 2420 reflections

  • 158 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.23 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3A⋯O4 0.84 (3) 2.16 (2) 2.6519 (15) 117 (2)
O3—H3A⋯O2i 0.84 (3) 2.20 (3) 2.9111 (16) 143 (2)
C9—H9B⋯Cg1ii 0.97 2.90 3.7483 (2) 146
C13—H13B⋯Cg1iii 0.96 2.96 3.688 (3) 134
Symmetry codes: (i) x+1, y+1, z; (ii) -x, -y+1, -z; (iii) -x, -y+2, -z. Cg1 is the centroid of the C3–C8 ring.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900806X/sj2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900806X/sj2576Isup2.hkl

checkCIF report


Comment top

Marine fungi have proven to be a rich source of novel structural compounds with interesting biological activities and a high level of biodiversity. As a continuation of our previous investigations aimed at finding new bioactive compounds, we found that an unidentified endophytic strain B60 isolated from the mangrove tree can produce new metabolites (Shao et al. 2007; Shao et al. 2008).

Although the structure of the title compound was previously elucidated on the basis of spectroscopic analysis (Shao et al. 2008), we have now determined its solid state structure, Fig. 1, which is reported here. All bond lengths and angles in the molecule are in good agreement with those reported in a related structure by Huang et al. (2005). In the title compound, the most striking feature is the interesting arrangement of the molecules, which linked to form a one-dimensional chain by intermolecular O—H···O hydrogen bonds, Table 1, Fig. 2. Further, weak non-classical C—H···π contacts, similar to those previously reported (Nangia, 2002; Umezawa et al. 1999) are also observed, in which C9—H9B and C13—H13B act as donors with the benzene ring as the acceptor.

Related literature top

For structures with C—H···O and C—H···π contacts, see: Nangia (2002); Umezawa et al. (1999). For new bioactive secondary metabolites from the endophytic strain B60, see: Shao et al. (2007, 2008). For an investigation of the endophytic fungus, see: Shao et al. (2008). For a related structure, see: Huang et al. (2005). Cg1 is the centroid of the C3–C8 ring.

Experimental top

An unidentified fungus (No. B60) was deposited in the School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, People's Republic of China. Strain No. B60 was cultivated without shaking in GYT medium (10 g of glucose, 2 g of peptone /L, 1 g of yeast extract /L, 2.5 g of NaCl, 1L of water) at 298 K for 4 weeks. The cultures (120 L) were filtered through cheesecloth. The filtrate was concentrated to 3 L below 323 K, then extracted five times by shaking with an equal volume of ethyl acetate. The extract was evaporated under reduced pressure below 323 K. The combined organic extracts were subjected to silica-gel column chromatography, eluting with petroleum ether/ethyl acetate (9:1, v:v), to yield the title compound, which was confirmed by spectral data including NMR and EI—MS. Crystals of the title compound were obtained by evaporation of an ethyl acetate solution.

Refinement top

All H atoms were positioned geometrically and treated as riding, with C—H bonding lengths constrained to 0.93 (aromatic CH), 0.96 Å (methyl CH3), 0.97 Å (methylene CH2), and O—H = 0.84 Å, and with Uĩso~(H) = 1.2Ueq(CH) or Uĩso~(H) = 1.5Ueq(CH3, methylene C or OH).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of (I) viewed down the b axis with hydrogen bonds drawn as dashed lines.
Methyl 3-hydroxy-4-(3-methylbut-2-enyloxy)benzoate top
Crystal data top
C13H16O4Z = 2
Mr = 236.26F(000) = 252
Triclinic, P1Dx = 1.255 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8401 (16) ÅCell parameters from 4817 reflections
b = 8.3899 (17) Åθ = 1.9–26.0°
c = 11.099 (2) ŵ = 0.09 mm−1
α = 100.655 (3)°T = 291 K
β = 98.771 (3)°Block, colorless
γ = 115.456 (3)°0.40 × 0.38 × 0.35 mm
V = 625.3 (2) Å3
Data collection top
Bruker APEXII CCD
diffractometer		2420 independent reflections
Radiation source: fine-focus sealed tube2058 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.964, Tmax = 0.968k = −10→10
4817 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.1024P)2 + 0.0667P]
where P = (Fo2 + 2Fc2)/3
2420 reflections(Δ/σ)max < 0.001
158 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
C13H16O4γ = 115.456 (3)°
Mr = 236.26V = 625.3 (2) Å3
Triclinic, P1Z = 2
a = 7.8401 (16) ÅMo Kα radiation
b = 8.3899 (17) ŵ = 0.09 mm−1
c = 11.099 (2) ÅT = 291 K
α = 100.655 (3)°0.40 × 0.38 × 0.35 mm
β = 98.771 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		2420 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2058 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.968Rint = 0.014
4817 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.161H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.23 e Å−3
2420 reflectionsΔρmin = −0.25 e Å−3
158 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1−0.4408 (3)0.2951 (3)0.50642 (16)0.0716 (5)
H1A−0.36970.34580.59440.107*
H1B−0.46810.16920.47840.107*
H1C−0.56160.30090.49600.107*
C2−0.4029 (2)0.34671 (19)0.30738 (14)0.0490 (4)
C3−0.2748 (2)0.46837 (17)0.24198 (13)0.0453 (3)
C4−0.0924 (2)0.61796 (19)0.30835 (13)0.0481 (4)
H4A−0.04740.64100.39550.058*
C50.02077 (19)0.73115 (19)0.24510 (13)0.0457 (3)
C6−0.04479 (19)0.69490 (18)0.11391 (13)0.0452 (3)
C7−0.2253 (2)0.5465 (2)0.04830 (14)0.0558 (4)
H7A−0.27020.5224−0.03890.067*
C8−0.3388 (2)0.4343 (2)0.11268 (14)0.0544 (4)
H8A−0.45970.33460.06820.065*
C90.0269 (2)0.7902 (2)−0.07071 (14)0.0557 (4)
H9A−0.08950.8036−0.09420.067*
H9B0.00030.6684−0.11690.067*
C100.1952 (2)0.9336 (2)−0.10072 (15)0.0578 (4)
H10A0.30611.0114−0.03420.069*
C110.1993 (2)0.9589 (2)−0.21421 (14)0.0546 (4)
C120.0315 (3)0.8410 (3)−0.32730 (17)0.0836 (6)
H12A−0.07250.7516−0.30260.125*
H12B0.07240.7793−0.38920.125*
H12C−0.01380.9160−0.36320.125*
C130.3751 (3)1.1067 (3)−0.2368 (2)0.0752 (5)
H13A0.47481.1741−0.15820.113*
H13B0.33871.1889−0.26990.113*
H13C0.42421.0518−0.29680.113*
O1−0.32509 (16)0.39913 (15)0.43211 (10)0.0640 (4)
O2−0.56125 (16)0.21602 (16)0.25485 (12)0.0702 (4)
O30.19557 (16)0.87793 (16)0.31218 (11)0.0663 (4)
H3A0.231 (4)0.943 (4)0.263 (2)0.102 (8)*
O40.08089 (14)0.81567 (13)0.06303 (9)0.0537 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0731 (11)0.0727 (11)0.0615 (10)0.0165 (9)0.0292 (9)0.0378 (9)
C20.0446 (7)0.0438 (7)0.0559 (8)0.0141 (6)0.0170 (6)0.0222 (6)
C30.0414 (7)0.0383 (7)0.0526 (8)0.0122 (6)0.0151 (6)0.0191 (6)
C40.0452 (7)0.0459 (7)0.0446 (7)0.0117 (6)0.0118 (6)0.0186 (6)
C50.0377 (7)0.0407 (7)0.0492 (7)0.0089 (5)0.0108 (5)0.0166 (6)
C60.0434 (7)0.0397 (7)0.0494 (8)0.0127 (6)0.0169 (6)0.0192 (6)
C70.0535 (8)0.0494 (8)0.0451 (7)0.0067 (7)0.0093 (6)0.0177 (6)
C80.0456 (7)0.0441 (7)0.0523 (8)0.0029 (6)0.0078 (6)0.0166 (6)
C90.0579 (9)0.0501 (8)0.0481 (8)0.0119 (7)0.0171 (6)0.0208 (6)
C100.0588 (9)0.0500 (8)0.0534 (8)0.0114 (7)0.0210 (7)0.0205 (7)
C110.0688 (10)0.0527 (8)0.0556 (8)0.0316 (8)0.0311 (7)0.0252 (7)
C120.0918 (14)0.0981 (15)0.0565 (10)0.0370 (12)0.0193 (10)0.0314 (10)
C130.0933 (14)0.0714 (11)0.0806 (12)0.0382 (11)0.0533 (11)0.0417 (10)
O10.0574 (6)0.0626 (7)0.0561 (6)0.0075 (5)0.0189 (5)0.0305 (5)
O20.0530 (7)0.0590 (7)0.0689 (7)−0.0030 (5)0.0148 (5)0.0275 (6)
O30.0486 (6)0.0604 (7)0.0555 (7)−0.0055 (5)0.0056 (5)0.0255 (5)
O40.0496 (6)0.0489 (6)0.0470 (6)0.0055 (5)0.0153 (4)0.0212 (5)
Geometric parameters (Å, º) top
C1—O11.4418 (17)C8—H8A0.9300
C1—H1A0.9600C9—O41.4289 (18)
C1—H1B0.9600C9—C101.489 (2)
C1—H1C0.9600C9—H9A0.9700
C2—O21.2066 (18)C9—H9B0.9700
C2—O11.3300 (18)C10—C111.319 (2)
C2—C31.4808 (18)C10—H10A0.9300
C3—C81.378 (2)C11—C121.484 (3)
C3—C41.399 (2)C11—C131.500 (2)
C4—C51.3763 (18)C12—H12A0.9600
C4—H4A0.9300C12—H12B0.9600
C5—O31.3594 (17)C12—H12C0.9600
C5—C61.397 (2)C13—H13A0.9600
C6—O41.3563 (16)C13—H13B0.9600
C6—C71.386 (2)C13—H13C0.9600
C7—C81.382 (2)O3—H3A0.84 (3)
C7—H7A0.9300
O1—C1—H1A109.5O4—C9—C10106.75 (12)
O1—C1—H1B109.5O4—C9—H9A110.4
H1A—C1—H1B109.5C10—C9—H9A110.4
O1—C1—H1C109.5O4—C9—H9B110.4
H1A—C1—H1C109.5C10—C9—H9B110.4
H1B—C1—H1C109.5H9A—C9—H9B108.6
O2—C2—O1123.26 (13)C11—C10—C9125.11 (15)
O2—C2—C3124.42 (14)C11—C10—H10A117.4
O1—C2—C3112.31 (12)C9—C10—H10A117.4
C8—C3—C4119.39 (13)C10—C11—C12121.92 (15)
C8—C3—C2118.91 (13)C10—C11—C13121.91 (16)
C4—C3—C2121.69 (13)C12—C11—C13116.16 (15)
C5—C4—C3120.19 (13)C11—C12—H12A109.5
C5—C4—H4A119.9C11—C12—H12B109.5
C3—C4—H4A119.9H12A—C12—H12B109.5
O3—C5—C4119.06 (13)C11—C12—H12C109.5
O3—C5—C6120.93 (12)H12A—C12—H12C109.5
C4—C5—C6120.01 (12)H12B—C12—H12C109.5
O4—C6—C7126.11 (13)C11—C13—H13A109.5
O4—C6—C5114.18 (12)C11—C13—H13B109.5
C7—C6—C5119.71 (13)H13A—C13—H13B109.5
C8—C7—C6119.92 (14)C11—C13—H13C109.5
C8—C7—H7A120.0H13A—C13—H13C109.5
C6—C7—H7A120.0H13B—C13—H13C109.5
C3—C8—C7120.78 (13)C2—O1—C1117.18 (12)
C3—C8—H8A119.6C5—O3—H3A105.7 (18)
C7—C8—H8A119.6C6—O4—C9118.40 (11)
O2—C2—C3—C80.9 (2)C5—C6—C7—C8−0.6 (2)
O1—C2—C3—C8−178.13 (12)C4—C3—C8—C7−0.3 (2)
O2—C2—C3—C4−179.95 (14)C2—C3—C8—C7178.79 (13)
O1—C2—C3—C41.0 (2)C6—C7—C8—C30.2 (3)
C8—C3—C4—C50.8 (2)O4—C9—C10—C11−177.76 (15)
C2—C3—C4—C5−178.28 (12)C9—C10—C11—C12−0.9 (3)
C3—C4—C5—O3178.57 (13)C9—C10—C11—C13−179.89 (15)
C3—C4—C5—C6−1.2 (2)O2—C2—O1—C1−1.6 (2)
O3—C5—C6—O40.8 (2)C3—C2—O1—C1177.47 (13)
C4—C5—C6—O4−179.48 (12)C7—C6—O4—C9−0.6 (2)
O3—C5—C6—C7−178.70 (14)C5—C6—O4—C9179.99 (12)
C4—C5—C6—C71.0 (2)C10—C9—O4—C6−176.59 (12)
O4—C6—C7—C8−179.96 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O40.84 (3)2.16 (2)2.6519 (15)117 (2)
O3—H3A···O2i0.84 (3)2.20 (3)2.9111 (16)143 (2)
C9—H9B···Cg1ii0.972.903.7483 (2)146
C13—H13B···Cg1iii0.962.963.688 (3)134
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC13H16O4
Mr236.26
Crystal system, space groupTriclinic, P1
Temperature (K)291
a, b, c (Å)7.8401 (16), 8.3899 (17), 11.099 (2)
α, β, γ (°)100.655 (3), 98.771 (3), 115.456 (3)
V (Å3)625.3 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.40 × 0.38 × 0.35
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.964, 0.968
No. of measured, independent and
observed [I > 2σ(I)] reflections		4817, 2420, 2058
Rint0.014
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.161, 1.05
No. of reflections2420
No. of parameters158
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.23, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O40.84 (3)2.16 (2)2.6519 (15)117 (2)
O3—H3A···O2i0.84 (3)2.20 (3)2.9111 (16)143 (2)
C9—H9B···Cg1ii0.972.903.7483 (2)146
C13—H13B···Cg1iii0.962.963.688 (3)134
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z.
 

Acknowledgements

We wish to acknowledge financial support from the National Natural Science Foundation of China (No. 40776073), the Basic Research Program of Science and Technology, Ministry of Science and Technology of China (No. 2007FY210500), the Youthful Fund of Guangdong Medical College (No. XQ0511), and the doctoral startup fund of Ocean University of China (No. 1404–82421036).

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ISSN: 2056-9890
Volume 65| Part 4| April 2009| Pages o734-o735
doi:10.1107/S160053680900806X
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